Vacation rentals in New Windsor, MD

178 available vacation rental offers

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Best Vacation rentals and Airbnb offers in New Windsor, MD

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV - New Windsor, MD

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Holiday Home, New Windsor

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV is a holiday home in New Windsor. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV is a holiday home in New Windsor. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $690.

From$80/night
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Songbird Cottage 3b, sleeps 6 - New Windsor, MD

Songbird Cottage 3b, sleeps 6

Holiday Home, New Windsor

Songbird Cottage 3b, sleeps 6 is a holiday home in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Songbird Cottage 3b, sleeps 6

Songbird Cottage 3b, sleeps 6 is a holiday home in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $854.

From$96/night
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The Loft at East Patrick - New Windsor, MD

The Loft at East Patrick

Apartment, New Windsor

The Loft at East Patrick is a apartment in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Loft at East Patrick

The Loft at East Patrick is a apartment in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $880.

From$96/night
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Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg - New Windsor, MD

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg

Country House, New Windsor

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg is a country house in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg is a country house in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,029.

From$116/night
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Browse Vacation Rentals with a Pool in New Windsor, MD

Add a pool to the search when you want an easy place to cool off between outings.

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. - New Windsor, MD

Resort studio apartment with private hot tub, fire pit, gym, and access to pool.

Apartment, New Windsor

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. is a apartment in New Windsor, with pool access. This stay gives travelers a comfortable base for exploring…

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About Resort studio apartment with private hot tub, fire pit, gym, and access to pool.

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. is a apartment in New Windsor, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, gym, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,144.

From$141/night
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Cozy Guesthouse in Woodstock, MD - New Windsor, MD

Cozy Guesthouse in Woodstock, MD

Cabin, New Windsor

Cozy Guesthouse in Woodstock, MD is a cabin in New Windsor, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD is a cabin in New Windsor, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,387.

From$153/night
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Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit - New Windsor, MD

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit

Country House, New Windsor

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit is a country house in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit is a country house in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,619.

From$176/night
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Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! - New Windsor, MD

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm!

Apartment, New Windsor

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! is a apartment in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm!

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! is a apartment in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$191/night
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Best New Windsor, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Golf Course Guest Suite in Gettysburg - New Windsor, MD

Golf Course Guest Suite in Gettysburg

Apartment, New Windsor

Golf Course Guest Suite in Gettysburg is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Golf Course Guest Suite in Gettysburg

Golf Course Guest Suite in Gettysburg is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,442.

From$113/night
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Apt Near the Metro w/ Easy Baltimore Access - New Windsor, MD

Apt Near the Metro w/ Easy Baltimore Access

Apartment, New Windsor

Apt Near the Metro w/ Easy Baltimore Access is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Apt Near the Metro w/ Easy Baltimore Access

Apt Near the Metro w/ Easy Baltimore Access is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,610.

From$133/night
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Gettysburg Farmstead Farm-Stays - New Windsor, MD

Gettysburg Farmstead Farm-Stays

Apartment, New Windsor

Gettysburg Farmstead Farm-Stays is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Gettysburg Farmstead Farm-Stays

Gettysburg Farmstead Farm-Stays is a apartment in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,187.

From$170/night
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Georges on York Boutique Inn - New Windsor, MD

Georges on York Boutique Inn

B & B, New Windsor

Georges on York Boutique Inn is a b & b in New Windsor, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Georges on York Boutique Inn

Georges on York Boutique Inn is a b & b in New Windsor, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, free wifi, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,628.

From$208/night
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Best New Windsor, MD vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. - New Windsor, MD

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square.

Apartment, New Windsor

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. is a apartment in New Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square.

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. is a apartment in New Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $721.

From$78/night
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Cool Smokehouse on historic Manor House grounds! - New Windsor, MD

Cool Smokehouse on historic Manor House grounds!

Country House, New Windsor

Cool Smokehouse on historic Manor House grounds! is a country house in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cool Smokehouse on historic Manor House grounds!

Cool Smokehouse on historic Manor House grounds! is a country house in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, and living room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $829.

From$89/night
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The Jarboe Suite on historic Manor House grounds! - New Windsor, MD

The Jarboe Suite on historic Manor House grounds!

Holiday Home, New Windsor

The Jarboe Suite on historic Manor House grounds! is a holiday home in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Jarboe Suite on historic Manor House grounds!

The Jarboe Suite on historic Manor House grounds! is a holiday home in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $829.

From$89/night
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Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown - New Windsor, MD

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Apartment, New Windsor

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a apartment in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a apartment in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $994.

From$106/night
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Our Favorite Family-Friendly Vacation Rentals in New Windsor, MD

Plan a trip with stays that give families more room to spread out.

A cozy and spacious house In the heart of Hereford county .Comfortable living . - New Windsor, MD

A cozy and spacious house In the heart of Hereford county .Comfortable living .

Holiday Home, New Windsor

A cozy and spacious house In the heart of Hereford county .Comfortable living . is a holiday home in New Windsor, with kitchen access. This stay gives travelers a comfortable base for…

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About A cozy and spacious house In the heart of Hereford county .Comfortable living .

A cozy and spacious house In the heart of Hereford county .Comfortable living . is a holiday home in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,278.

From$113/night
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Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA - New Windsor, MD

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Cottage, New Windsor

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA is a cottage in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA is a cottage in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,090.

From$113/night
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Peaceful Getaway w/ Countryside Views in Upperco - New Windsor, MD

Peaceful Getaway w/ Countryside Views in Upperco

Cottage, New Windsor

Peaceful Getaway w/ Countryside Views in Upperco is a cottage in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peaceful Getaway w/ Countryside Views in Upperco

Peaceful Getaway w/ Countryside Views in Upperco is a cottage in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,604.

From$172/night
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Rural & Historic Detour Escape w/ Horses On-site! - New Windsor, MD

Rural & Historic Detour Escape w/ Horses On-site!

Cottage, New Windsor

Rural & Historic Detour Escape w/ Horses On-site! is a cottage in New Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site! is a cottage in New Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,989.

From$233/night
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